I put my daughter in a toddler bed when she was 2.5 years and she wears pyjamas to bed. For bedding she has a pillow, sheet and doona. Now that it is winter I make sure she wears really warm pyjamas as her bedroom gets really cold at night.

When we moved our kids to beds we bought the kids tontine pillows which are much flatter and designed for kids - they have a blue print on white and can be bought from Target.
We stopped using sleeping bags at this point and put on the sleep suits instead over the top of their pyjamas. You can layer as much as is needed.
As for getting out of bed - we have the rule that we put them in and out to avoid the midnight toddle into our bedroom - our bedrooms are all close together, so we can hear them if they need us, and our eldest two at nearly 5 and 3 know they can get out and go to the loo as needed or can come and grab us if important. Our boys attempted to get out a few times when they started in a big bed and we just popped them back in, explained the rules and it was all good. Our DD is yet to test the theory out - but it's only been about a month so far!

They're ok to have a pillow from 2 years, I don't think they actually *need* one though, but its no longer a SIDS risk. My DS had a flatter toddler one from 2 years and we switched to a fleece sleep suit with legs in winter. He's 3.5 and we still haven't managed to get him in the toddler bed yet though, he still prefers mummy's bed

Our 19mo dd showed a preference for pillows a few months ago so I gave her a triangle/V pillow (reasonably flat) when she had a cold and she loves it, so it stayed. She goes to sleep in a sleeping bag over a long arm/leg bodysuit or pj's, but she's recently started unzipping the sleeping bag if she doesn't want to sleep (usually in the morning, but sometimes at night). So, I've recently introduced a lightweight blanket over her to see if I could transition her to blankets instead of a sleeping bag, eventhough she's still in her cot. I imagine she'll be in toddler bed (the cot converts to a toddler bed) by the end of this year.

Hmm maybe we'll get rid of the sleeping bag. We've been doing things like putting her Dora doll to bed and tucking it in so she's starting to get the idea of using blankets. She also likes resting her head on the cushions in the lounge room so maybe she'll like having a pillow. I'm just paranoid about the SIDS thing but if it's safe from 2yrs we might get her one then.

I had no intention of putting her in a bed this young but she's started waking constantly at night and hates being put back in her cot.

Both my DD's went into a bed at 18months and were in sleeping bags and had no problems. The beds were low to the ground so they just climbed in and out they had no issues walking in the sleeping bag either lol.

As for pillows we bought junior pillows from pillow talk and they are flat as anything, basically the thickness of a pillow protector. They got them when they went into beds and have had no isssues.

My youngest is now 2.5 and still doesn't really stay under her blankets very well but I just dress her warmly. At the moment she sleeps in singlet socks thermal skivy and footed thermal pants then flannel pj's over the top. She doesn't seem to get too cold, and we don't have heaters

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